Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines

Detalhes bibliográficos
Autor(a) principal: Carvalho,Marcia de
Data de Publicação: 1999
Outros Autores: Sorrilha,Ana E.P.M., Rodrigues,J. Augusto R.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531999000500012
Resumo: We describe in this paper the action of trifluoroacetic acid, trifluoromethanesulfonic acid and aluminum chloride upon ortho-substituted aryl azides to form indoles, azepines and arylamines in good yields. The protonated azides lose nitrogen to form arylnitrenium ion intermediates which undergo intramolecular aromatic N-substitution. The acid decomposition of aryl azides is compared with reported thermolyses.
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spelling Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylaminesnitrenium ionaryl azidesindolesazepinesWe describe in this paper the action of trifluoroacetic acid, trifluoromethanesulfonic acid and aluminum chloride upon ortho-substituted aryl azides to form indoles, azepines and arylamines in good yields. The protonated azides lose nitrogen to form arylnitrenium ion intermediates which undergo intramolecular aromatic N-substitution. The acid decomposition of aryl azides is compared with reported thermolyses.Sociedade Brasileira de Química1999-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531999000500012Journal of the Brazilian Chemical Society v.10 n.5 1999reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50531999000500012info:eu-repo/semantics/openAccessCarvalho,Marcia deSorrilha,Ana E.P.M.Rodrigues,J. Augusto R.eng2001-06-07T00:00:00Zoai:scielo:S0103-50531999000500012Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2001-06-07T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines
title Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines
spellingShingle Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines
Carvalho,Marcia de
nitrenium ion
aryl azides
indoles
azepines
title_short Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines
title_full Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines
title_fullStr Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines
title_full_unstemmed Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines
title_sort Reaction of aromatic azides with strong acids: formation of fused nitrogen heterocycles and arylamines
author Carvalho,Marcia de
author_facet Carvalho,Marcia de
Sorrilha,Ana E.P.M.
Rodrigues,J. Augusto R.
author_role author
author2 Sorrilha,Ana E.P.M.
Rodrigues,J. Augusto R.
author2_role author
author
dc.contributor.author.fl_str_mv Carvalho,Marcia de
Sorrilha,Ana E.P.M.
Rodrigues,J. Augusto R.
dc.subject.por.fl_str_mv nitrenium ion
aryl azides
indoles
azepines
topic nitrenium ion
aryl azides
indoles
azepines
description We describe in this paper the action of trifluoroacetic acid, trifluoromethanesulfonic acid and aluminum chloride upon ortho-substituted aryl azides to form indoles, azepines and arylamines in good yields. The protonated azides lose nitrogen to form arylnitrenium ion intermediates which undergo intramolecular aromatic N-substitution. The acid decomposition of aryl azides is compared with reported thermolyses.
publishDate 1999
dc.date.none.fl_str_mv 1999-10-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531999000500012
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531999000500012
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50531999000500012
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.10 n.5 1999
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
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instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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